Diisopropylethylamine → HCID 53924266, compound

HRID 1789904Notes

Reaction equation

HRID 1789904 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[C:5]([CH2:7]Br)=[CH2:6])[CH3:2].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C>CN(C)C=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH2:7][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])=[CH2:6])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 3106202-(Bromomethyl)acrylic acid ethyl ester

Product 1

HCID 53924266HCID 53924266, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromomethyl-acrylic acid ethyl ester (1.93 g, 10 mmol) in N,N-dimethylformamide (25 mL) was added piperazine-1-carboxylic acid tert-butyl ester (1.86 g, 10 mmol) and then, dropwise, ethyl-diisopropyl-amine (1.71 mL, 10 mmol). After stirring for 16 h at room temperature the solvent was removed under reduced pressure and water (50 mL) and dichloromethane (50 mL) were added. After stirring for 2 min the layers were separated, the organic was washed with water and brine, and dried over magnesium sulphate. The solvent was removed under reduced pressure to give crude 4-(2-ethoxycarbonyl-allyl)-piperazine-1-carboxylic acid tert-butyl ester (2.456 g, 82%).

Workup

  1. customwas removed under reduced pressure and water (50 mL) and dichloromethane (50 mL)
  2. additionwere added
  3. stirringAfter stirring for 2 min the layers
  4. customwere separated
  5. washthe organic was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e0f29dfe808d49c1ba266330dd8f52c3
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…